Two Ways: Menswear-Inspired Pumps

Shoes: Boden T-Strap Pumps ($149)

From the Left, Ring: Elizabeth & James Crossband Ring ($95) Watch: Michael Kors Chronograph Watch ($250) Blouse: Thomas Mason Tuxedo Shirt ($158) Bag: Asos Vintage Briefcase ($107) Jacket: Mango Tailored Blazer ($55) Pants: Moschino Trousers ($605)

From Right, Necklace: Kate Spade Triple Strand Necklace ($73) Ring: Pandora Rhodolite Ring ($100) Bag: Asos Smart Boxy Bag ($68) Sweater: Iris & Ink Cashmere Sweater ($168) Skirt: Double Serge Skirt ($98)

For the Office. I wanted to do something a bit more masculine to complement the shoes, so I chose a classic navy pinstripe pants and a navy blazer.  My preference would have been to find a full pinstripe pantsuit.  Theory makes a lovely one (jacket, pants).  Ann Taylor makes a nice one in the Hill Staffer price range (jacket, pants).  If you need something less expensive, NY & Co has well-priced pinstripe suit separates (pants, jacket).

The blouse I chose is a tuxedo shirt from J.Crew. If you want something a bit more feminine, they also sell a tuxedo shirt in the Swiss Dot print.  It’s lovely but runs a bit big.  You might also consider a simple white button up.  I’ve always been a big fan of the Banana Republic tops.  Plus-size ladies should try this Ralph Lauren button-up blouse. 

I accented the outfit with simple gold jewelry (you could swap in silver if you prefer).  This big watch is a great piece but if you’d like something less expensive, this KL watch has a similar look.  As for the ring, Topshop makes a similar piece for $15.  And for the bag, I chose a men’s briefcase in a vintage style.  Looking for something similar?  Antique stores and thrift shops are a great place to find old briefcases.

For the hair, I would wear it down and in waves, an updo might be too severe.  For the nails, I would choose a berry shade for the lips (Clinique Broadest Berry) and nails and a rosy, but not pink, cheek like Jouer rose blush.

For the Office.  It’s been awhile since I’ve shown one of my favorite styling ideas on the blog: monochromatic outfits.  I love when people mix different shades of the color.  When done in the right way, it can be quite elegant.

This outfit is a combination of greys: a pencil skirt, a cashmere sweater and a chunky necklace.  The skirt above is J.Crew, but this Halogen pencil is less expensive and good quality.  If you’re looking for a less expensive sweater, this cashmere one from the Neiman Marcus store brand and this peplum Ann Taylor are good choices.

If the Kate Spade (currently 50%-off) is still more than you want to spend on a necklace, this marbled bib necklace from The Limited might be a good choice.  Or you could try a set of faux-grey pearls a la Diane Lockhart on The Good Wife.

To bring a bit of color into the outfit, I chose this silver ring with Rhodolite accents to complement the berry color in the skirt.  I like the twisted metal, it reminds me of David Yurman’s pieces.  I also added a teal bag to bring in another fall hue, and at this price, why not start carrying a colorful winter bag?

For the hair, I would wear it up in a Gibson roll or maybe a braided updo (I never learned how to braid, so that’s out for me. Sad face.).  For the makeup, I would stick to a similar color palette as the first outfit, but I would add a good coat of liquid eyeliner and a heavier handed mascara application.  You need color on your face to offset the monochromatic palette, so deepening the eye is important and do not forget the lipstick!